CN104892840B - A kind of phenylethene modified dicyclopentadiene petroleum resin and preparation method thereof - Google Patents
A kind of phenylethene modified dicyclopentadiene petroleum resin and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of phenylethene modified dicyclopentadiene petroleum resin and preparation method thereof, belongs to technical field of petrochemical industry.A kind of phenylethene modified dicyclopentadiene petroleum resin of the present invention, its softening point are 90 130 DEG C, and Gardner Color is 45, and weight average molecular weight is 400 1000, and molecular weight distributing index is 1.5 2.5；A kind of method for preparing above-mentioned phenylethene modified dicyclopentadiene petroleum resin of the present invention, its step is：The mixing of reaction raw materials, the hot polymerization reaction of reaction raw materials and purification.Mixed with high-purity cyclopentadiene monomer and styrene monomer as raw material in the present invention, by the proportioning for adjusting each component, and strictly control the various technological parameters of hot polymerization reaction, such that it is able to prevent the generation being crosslinked in hot polymerization process, the performances such as the compatibility of dissolubility, colourity and elastomer of phenylethene modified dicyclopentadiene petroleum resin are made to significantly improve.
Description
Technical field
The invention belongs to technical field of petrochemical industry, more particularly, it relates to a kind of phenylethene modified dicyclopentadiene
Petropols and preparation method thereof.
Background technology
Petropols are that, with the C5 of cracking of ethylene byproduct in process, C9 fractions are a kind of thermoplastic of main polymerizable raw material
Property resin.Wherein, dicyclopentadiene petroleum resin is set made by with the dicyclopentadiene in C5 fraction as primary raw material
Fat, cheap and easily-available with raw material, softening point is high, and rigidity is strong, the advantages of brightness is high, thus is widely used in compounding rubber, oil
The fields such as black auxiliary agent, paint and binding agent, but as which there is also form and aspect depth simultaneously, cohesive force is poor, with elastomer material
The shortcomings of compatibility of material is poor, so as to limit its use range.Therefore, the modification to dicyclopentadiene petroleum resin
Into the focus of common concern in the industry.
Styrene and its derivatives, such as α-methyl styrene, are a kind of aromatic contents, are added to dicyclopentadiene oil
In resin structure, can effectively improve its dissolubility and thickening property, particularly in PUR with elastomer (such as SIS and
SBS etc.) consistency problem can be very significantly improved, therefore, Styrene and its derivatives have been widely used for bicyclic penta
The modification of diene Petropols.
It is typically with thick dicyclopentadiene as raw material in prior art, dicyclopentadiene is produced using the method for thermal polymerization
Petropols, and when being modified process to dicyclopentadiene petroleum resin using styrene compound, usually by benzene second
Vinyl compound is mixed with dicyclopentadiene feedstock, is allowed to be copolymerized together.Due in the method production process
Introducing without catalyst, will not bring the environmental problems such as liquid waste processing because of the removing of catalyst, but when being produced using the method,
Heat polymerization temperature and pressure are higher, and in the course of the polymerization process, styrene is easily crosslinked with dicyclopentadiene feedstock and generates many
The polymer that cannot be dissolved, these polymer can only be removed by filtering, and are not only created a large amount of reluctant solids and are given up
Expect, and these polymer are difficult to remove completely, so as to affect the normal use of modified dicyclopentadiene petroleum resin.
Jing is retrieved, Chinese Patent Application No.：01820355.8, the applying date：December 07 calendar year 2001, invention and created name
For：From the thermally polymerized copolymers that styrene and dicyclopentadiene monomers are manufactured, this application case discloses a kind of styrene of hydrogenation
Modified bicyclopentadiene Petropols and its manufacture method, which is first before being hydrogenated with to bicyclopentadiene Petropols
Process is modified using styrene to resin, there is the bicyclopentadiene Petropols after making to be modified enough aromatic hydrocarbon to contain
Amount, molecular weight are relatively low, and color is relatively shallower, only need less harsh hydroconversion condition obtain the viscosifier tree of shallower colourity
Fat.This application case be one kind styrene mix with dicyclopentadiene monomers after together with carry out hot polymerization react come to bicyclo- penta 2
Alkene Petropols are modified the scheme of process, but due to due to above-mentioned analysis so that the colourity of modified product and stable
Property be affected, make follow-up hydrogenation process effect decrease.
The content of the invention
1. invention technical problem to be solved
It is an object of the invention to directly mixed with thick dicyclopentadiene using styrene compound in overcoming prior art
Close, when carrying out hot polymerization reaction modifying, easily generate substantial amounts of insoluble polymer, the dissolubility and colourity of gained Petropols is poor
Deficiency, there is provided a kind of phenylethene modified dicyclopentadiene petroleum resin and preparation method thereof.There is provided using the present invention
Technical scheme, is prevented from styrene compound and crosslinks reaction with dicyclopentadiene feedstock, produce modified resin
Product have preferable dissolubility and thickening property, while improving the form and aspect of resin.
2. technical scheme
To reach above-mentioned purpose, the technical scheme that the present invention is provided is：
First, a kind of phenylethene modified dicyclopentadiene petroleum resin of the present invention, the dicyclopentadiene petroleum resin
Softening point be 90-130 DEG C, Gardner Color is 4-5, and weight average molecular weight is 400-1000, and molecular weight distributing index is 1.5-
2.5。
Second, the preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the present invention, its step is：
The mixing of step one, reaction raw materials：
High-purity cyclopentadiene monomer, styrene monomer and atent solvent are carried out being mixed to form mixed liquor；
The hot polymerization reaction of step 2, reaction raw materials：
Under nitrogen protection, mixed liquor is heated under stirring condition to 200-250 DEG C, control pressure is carried out in below 2MPa
Hot polymerization reacts 3-8 hours；
Step 3, purification：
After hot polymerization reaction terminates, purified process dicyclopentadiene petroleum resin phenylethene modified needed for obtaining final product.
Further, in mixed liquor described in step one, the mass fraction of three kinds of components is as follows：
Atent solvent 30-60 parts；
High-purity cyclopentadiene monomer 40-60 parts；
Styrene monomer 10-30 parts.
Further, described high-purity cyclopentadiene monomer is made up of the component of following mass percent：Ring penta 2
Alkene>90%；Dicyclopentadiene<10%；Other<0.1%.
Further, in described high-purity cyclopentadiene monomer, the mass percent of cyclopentadiene is more than 99%.
Further, the atent solvent in step one selects the solvent naphtha of benzene,toluene,xylene or saturation.
Further, during the styrene monomer in step one is styrene, methyl styrene and α-methyl styrene
One kind, or two or more combination.
Further, atent solvent is removed using vacuum distillation in step 3 and unreacted monomer is purified.
3. beneficial effect
The technical scheme provided using the present invention, compared with prior art, with following remarkable result：
(1) preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the invention, which is with phenylethylene
Monomer and high-purity cyclopentadiene monomer carry out hot polymerization reaction for raw material, due to cyclopentadiene in the cyclopentadiene monomers that used
Mass percent be more than 90%, hot polymerization reaction can carry out at a lower temperature, so as to effectively prevent cross-linking reaction
Occur, be greatly reduced the quantity of insoluble polymer, it is ensured that the normal use of Petropols；Meanwhile, hot polymerization reaction temperature
The reduction of degree, moreover it is possible to make preparation Petropols colourity be improved significantly.
(2) preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the invention is suitable by selecting
Styrene monomer, and strictly control styrene monomer, high-purity cyclopentadiene monomer and atent solvent in mixed liquor
Proportioning, and coordinate the hot polymerization reaction process parameter of optimization so that the phenylethene modified dicyclopentadiene petroleum resin product of preparation
The performance such as the compatibility of dissolubility, thickening property and elastomer (such as SIS and SBS etc.) it is phenylethene modified compared to common
Dicyclopentadiene petroleum resin is significantly improved.
Specific embodiment
To further appreciate that present disclosure, with reference to embodiment, the invention will be further described.
Embodiment 1
The preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the present embodiment, its step is：
The mixing of step one, reaction raw materials：
High-purity cyclopentadiene monomer, styrene monomer and atent solvent are carried out being mixed to form mixed liquor, the mixing
In liquid, the mass fraction of three kinds of components is respectively：30 parts of atent solvent, 60 parts of high-purity cyclopentadiene monomer, styrene monomer
25 parts；High-purity cyclopentadiene monomer in the present embodiment is the dicyclopentadiene industry with commercially available mass percent about 80%
Product is raw material, adds it in the atmospheric distillation tower tower reactor that a number of theoretical plate is 15, and bottom temperature is heated to 200
DEG C, the fraction of 41-44 DEG C from tower top as collected by 2 reflux ratio.The final high-purity cyclopentadiene monomer for obtaining include as
The component of lower mass percent：Cyclopentadiene 92%, dicyclopentadiene 7.95%, other 0.05%.Styrene in the present embodiment
Class monomer selects styrene, atent solvent to select benzene.
The hot polymerization reaction of step 2, reaction raw materials：
Under nitrogen protection, mixed liquor is placed in autoclave, mixed liquor is heated under stirring condition to 250 DEG C, reactor
It is interior for self-generated pressure, control its pressure for 1.8MPa, carry out hot polymerization and react 7 hours.
What deserves to be explained is, due to hot polymerization being carried out as raw material with high-purity cyclopentadiene monomer and styrene in the present embodiment
Reaction, in cyclopentadiene monomers, the mass percent of cyclopentadiene is higher, so that hot polymerization reaction can be at a lower temperature
Carry out, effectively prevent the generation of cross-linking reaction, be greatly reduced the quantity of insoluble polymer, it is ensured that Petropols
It is normal to use；Meanwhile, the reduction of hot polymerization reaction temperature is also obviously improved the colourity of the Petropols of preparation.Additionally,
The use of the high-purity cyclopentadiene monomer in the present embodiment is raw material, the condition such as temperature, pressure when can also make thermal polymerization is more
Gently, the molecular structure of the phenylethene modified dicyclopentadiene petroleum resin of preparation is more homogeneous, and molecular weight is less, so that benzene second
The dissolubility of the modified dicyclopentadiene petroleum resin of alkene, colourity and it is further improved with the compatibility of elastomer.
Step 3, purification：
After hot polymerization reaction terminates, Jing vacuum distillations remove atent solvent and unreacted monomer, phenylethene modified needed for obtaining final product
Dicyclopentadiene petroleum resin, its softening point is 120 DEG C, and Gardner Color is 5, and weight average molecular weight is 1000, molecular weight point
Cloth index is 1.8.
Embodiment 2
The preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the present embodiment, its step is：
The mixing of step one, reaction raw materials：
High-purity cyclopentadiene monomer, styrene monomer and atent solvent are carried out being mixed to form mixed liquor, the mixing
In liquid, the mass fraction of three kinds of components is respectively：46 parts of atent solvent, 45 parts of high-purity cyclopentadiene monomer, styrene monomer
18 parts.High-purity cyclopentadiene monomer in the present embodiment is, with commercially available nine industrial products of carbon as raw material, to add it to one
During number of theoretical plate is 15 atmospheric distillation tower tower reactor, entered using the technique in the Chinese patent of Application No. CN200510025319
Prepared by row.The final high-purity cyclopentadiene monomer for obtaining includes the component of following mass percent：Cyclopentadiene 99.2%,
Dicyclopentadiene 0.71%, other 0.09%.In the present embodiment, styrene monomer selects styrene, atent solvent to select first
Benzene.
The hot polymerization reaction of step 2, reaction raw materials：
Under nitrogen protection, mixed liquor is placed in autoclave, mixed liquor is heated under stirring condition to 230 DEG C, reactor
It is interior for self-generated pressure, control its pressure for 2MPa, carry out hot polymerization and react 5 hours.
Step 3, purification：
After hot polymerization reaction terminates, Jing vacuum distillations remove atent solvent and unreacted monomer, phenylethene modified needed for obtaining final product
Dicyclopentadiene petroleum resin, its softening point be 106 DEG C, Gardner Color is 4, and weight average molecular weight is 850, molecular weight distribution
Index is 1.8, due to the mass percent of cyclopentadiene in high-purity cyclopentadiene monomer in the present embodiment it is relatively higher, and heat
The technological parameter of poly- reaction more optimizes, therefore, the colourity of the phenylethene modified dicyclopentadiene petroleum resin of preparation, dissolving
Property etc. combination property be better than embodiment 1.
Embodiment 3
The preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the present embodiment, its step is：
The mixing of step one, reaction raw materials：
High-purity cyclopentadiene monomer, styrene monomer and atent solvent are carried out being mixed to form mixed liquor, the mixing
In liquid, the mass fraction of three kinds of components is respectively：46 parts of atent solvent, 45 parts of high-purity cyclopentadiene monomer, styrene monomer
18 parts.High-purity cyclopentadiene monomer in the present embodiment is, with commercially available ten industrial products of carbon as raw material, to add it to one
During number of theoretical plate is 15 atmospheric distillation tower tower reactor, entered using the technique in the Chinese patent of Application No. CN200510025319
Prepared by row.The final high-purity cyclopentadiene monomer for obtaining includes the component of following mass percent：Cyclopentadiene 99.7%,
Dicyclopentadiene 0.26%, other 0.04%.In the present embodiment, styrene monomer selects methyl styrene, styrene and α-first
The cinnamic mixture of base, atent solvent select hexamethylene.
The hot polymerization reaction of step 2, reaction raw materials：
Under nitrogen protection, mixed liquor is placed in autoclave, mixed liquor is heated under stirring condition to 205 DEG C, reactor
It is interior for self-generated pressure, control its pressure for 1.6MPa, carry out hot polymerization and react 4 hours.
Step 3, purification：
After hot polymerization reaction terminates, Jing vacuum distillations remove atent solvent and unreacted monomer, phenylethene modified needed for obtaining final product
Dicyclopentadiene petroleum resin, its softening point be 130 DEG C, Gardner Color is 4, and weight average molecular weight is 400, molecular weight distribution
Index is 1.5.
Embodiment 4
The preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the present embodiment, its step is：
The mixing of step one, reaction raw materials：
High-purity cyclopentadiene monomer, styrene monomer and atent solvent are carried out being mixed to form mixed liquor, the mixing
In liquid, the mass fraction of three kinds of components is respectively：60 parts of atent solvent, 40 parts of high-purity cyclopentadiene monomer, styrene monomer
30 parts.The preparation method of the high-purity cyclopentadiene monomer in the present embodiment is with embodiment 1.The final high-purity ring penta 2 for obtaining
Alkene monomer includes the component of following mass percent：Cyclopentadiene 94%, dicyclopentadiene 5.93%, other 0.07%.This reality
In applying example, styrene monomer selects methyl styrene, atent solvent to select dimethylbenzene.
The hot polymerization reaction of step 2, reaction raw materials：
Under nitrogen protection, mixed liquor is placed in autoclave, mixed liquor is heated under stirring condition to 200 DEG C, reactor
It is interior for self-generated pressure, control its pressure for 1.7MPa, carry out hot polymerization and react 3 hours.
Step 3, purification：
After hot polymerization reaction terminates, Jing vacuum distillations remove atent solvent and unreacted monomer, phenylethene modified needed for obtaining final product
Dicyclopentadiene petroleum resin, its softening point be 90 DEG C, Gardner Color is 4, and weight average molecular weight is 1000, molecular weight distribution
Index is 2.5.
Embodiment 5
The preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the present embodiment, its step is：
The mixing of step one, reaction raw materials：
High-purity cyclopentadiene monomer, styrene monomer and atent solvent are carried out being mixed to form mixed liquor, the mixing
In liquid, the mass fraction of three kinds of components is respectively：35 parts of atent solvent, 54 parts of high-purity cyclopentadiene monomer, styrene monomer
22 parts.The preparation method of the high-purity cyclopentadiene monomer in the present embodiment is with embodiment 2, the final high-purity ring penta 2 for obtaining
Alkene monomer includes the component of following mass percent：Cyclopentadiene 96.4%, dicyclopentadiene 3.53%, other 0.07%.This
In embodiment, styrene monomer selects methyl styrene and cinnamic mixture, atent solvent to select hexane.
The hot polymerization reaction of step 2, reaction raw materials：
Under nitrogen protection, mixed liquor is placed in autoclave, mixed liquor is heated under stirring condition to 215 DEG C, reactor
It is interior for self-generated pressure, control its pressure for 1.5MPa, carry out hot polymerization and react 7 hours；
Step 3, purification：
After hot polymerization reaction terminates, Jing vacuum distillations remove atent solvent and unreacted monomer, phenylethene modified needed for obtaining final product
Dicyclopentadiene petroleum resin, its softening point be 127 DEG C, Gardner Color is 5, and weight average molecular weight is 600, molecular weight distribution
Index is 1.8.
Embodiment 6
The preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin of the present embodiment, its step is：
The mixing of step one, reaction raw materials：
High-purity cyclopentadiene monomer, styrene monomer and atent solvent are carried out being mixed to form mixed liquor, the mixing
In liquid, the mass fraction of three kinds of components is respectively：48 parts of atent solvent, 52 parts of high-purity cyclopentadiene monomer, styrene monomer
10 parts.The preparation method of the high-purity cyclopentadiene monomer in the present embodiment is with the 3 final high-purity ring penta 2 for obtaining of embodiment
Alkene monomer includes the component of following mass percent：Cyclopentadiene 95%, dicyclopentadiene 4.97%, other 0.03%.This reality
In applying example, styrene monomer selects α-methyl styrene, atent solvent to select toluene.
The hot polymerization reaction of step 2, reaction raw materials：
Under nitrogen protection, mixed liquor is placed in autoclave, mixed liquor is heated under stirring condition to 250 DEG C, reactor
It is interior for self-generated pressure, control its pressure for 1.8MPa, carry out hot polymerization and react 8 hours.
Step 3, purification：
After hot polymerization reaction terminates, Jing vacuum distillations remove atent solvent and unreacted monomer, phenylethene modified needed for obtaining final product
Dicyclopentadiene petroleum resin, its softening point be 112 DEG C, Gardner Color is 4, and weight average molecular weight is 900, molecular weight distribution
Index is 1.7.
The species of atent solvent, the technological parameter with the reaction of when hot polymerization between each reaction monomers is for the styrene for preparing
The performance of modified dicyclopentadiene petroleum resin has a major impact.Atent solvent used in the present invention and reaction monomers it
Between the compatibility preferably, by styrene monomer, high-purity cyclopentadiene monomer and atent solvent in strict control mixed liquor
Proportioning, and according to the proportioning between each component, hot polymerization reaction process parameter is optimized, so that the styrene for preparing
Compatibility of dissolubility, thickening property and elastomer (such as SIS and SBS etc.) of modified dicyclopentadiene petroleum resin product etc.
Performance is improved significantly compared to common phenylethene modified dicyclopentadiene petroleum resin.
Below schematically the present invention and embodiments thereof are described, the description does not have restricted, in the present invention
The saturated solvent Chuck Steak that can use of atent solvent, as long as which is with the reaction monomers compatibility preferably, and with reaction monomers not
React, because length is limited, no longer list one by one here.And high-purity cyclopentadiene monomer used in the present invention
Preparation method be not only limited to the method that embodiment 1-6 is mentioned, as long as can prepare meet the high-purity of condition of the present invention
The prior art of degree cyclopentadiene monomers.So, if one of ordinary skill in the art is enlightened by which, without departing from this
In the case of innovation and creation objective, the frame mode similar to the technical scheme and embodiment are designed without creative,
Protection scope of the present invention should be belonged to.
Claims (5)
1. a kind of preparation method of phenylethene modified dicyclopentadiene petroleum resin, its step is：
The mixing of step one, reaction raw materials：
High-purity cyclopentadiene monomer, styrene monomer and atent solvent are carried out being mixed to form mixed liquor, described is high-purity
Degree cyclopentadiene monomers are made up of the component of following mass percent：Cyclopentadiene>90%；Dicyclopentadiene<10%；Other<
0.1%；In the mixed liquor, the mass fraction of three kinds of components is as follows：
Atent solvent 30-60 parts；
High-purity cyclopentadiene monomer 40-60 parts；
Styrene monomer 10-30 parts；
The hot polymerization reaction of step 2, reaction raw materials：
Under nitrogen protection, mixed liquor is heated under stirring condition to 200-250 DEG C, control pressure carries out hot polymerization in below 2MPa
Reaction 3-8 hours；
Step 3, purification：
After hot polymerization reaction terminates, purified process dicyclopentadiene petroleum resin phenylethene modified needed for obtaining final product, this bicyclic penta
The softening point of diene Petropols is 90-130 DEG C, and Gardner Color is 4-5, and weight average molecular weight is 400-1000, molecular weight point
Cloth index is 1.5-2.5.
2. the preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin according to claim 1, its feature
It is：In described high-purity cyclopentadiene monomer, the mass percent of cyclopentadiene is more than 99%.
3. the preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin according to claim 2, its feature
It is：Atent solvent in step one selects the solvent naphtha of benzene,toluene,xylene or saturation.
4. the preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin according to claim 2, its feature
It is：Styrene monomer in step one be styrene, methyl styrene and α-methyl styrene in one kind, or two kinds with
On combination.
5. the preparation method of a kind of phenylethene modified dicyclopentadiene petroleum resin according to claim 4, its feature
It is：Atent solvent is removed using vacuum distillation in step 3 and unreacted monomer is purified.
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| CN106866905B (en) * | 2017-03-31 | 2019-08-30 | 安徽同心化工有限公司 | A kind of modified dicyclopentadiene petroleum resin of isoprene and preparation method |
| CN113336891B (en) * | 2021-06-22 | 2022-10-28 | 大庆华科股份有限公司 | Methyl styrene and indene modified dicyclopentadiene petroleum resin and preparation method thereof |
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| CN1183420A (en) * | 1996-11-27 | 1998-06-03 | 出光石油化学株式会社 | Copolymer, hydrogenated product thereof, and process for producing the same |
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|---|---|---|---|---|
| EP0455105A2 (en) * | 1990-04-24 | 1991-11-06 | Hercules Incorporated | Light colored, aromatic-modified piperylene resins |
| CN1183420A (en) * | 1996-11-27 | 1998-06-03 | 出光石油化学株式会社 | Copolymer, hydrogenated product thereof, and process for producing the same |
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| DCPD/苯乙烯共聚树脂的热分析研究;李爱元等;《中国胶粘剂》;20100831;第19卷(第8期);第10-14页，尤其1.3节 * |
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